


Beautiful Boy

by Gizmo83



Category: Supernatural
Genre: Other, Pretty! Dean, Teen Dean, Young Sam
Language: English
Status: In-Progress
Published: 2016-10-28
Updated: 2018-01-19
Packaged: 2018-08-27 15:01:18
Rating: Teen And Up Audiences
Warnings: Underage
Chapters: 10
Words: 10,493
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8406214
Author URL: https://archiveofourown.org/users/Gizmo83/pseuds/Gizmo83
Summary: Sam is sometimes in awe of his big brother and other times jealous of him.  Dean hates the way looks, except when it comes to the way hot girls look at him.Author’s Note: We know from the show that Sam was a short and chubby 12-year-old, so please keep that in mind for this story as Sam is 12 and Dean is 16.





	1. Chapter One

Chapter One:  
Sam headed towards where Dean had said to wait for him after school. In, whatever the name of this small town they were in, the population was small so they were in the same school… a Jr/Sr. High school. Sam a lowly seventh grader and Dean almost at the top in eleventh grade. Sam looked and saw a pretty brunette twirling her hair and giggling while she was talking to Dean. Sam sighed, Dean was lucky he was charismatic and made friends easily and Dean had good looks, which made it even easier for him, especially from the females. Sam watched his older brother be the epitome of cool and casual as he smiled slowly for the girl… Dean didn’t like to show off his smile all at once, said that the slow smirk dropped girls panties like nothing, of course that statement always set Sam into a fit of flushed faced giggles. When Dean did smile, a real smile, it was like the sun shining through the clouds after a deep and heavy rain. Dean noticed Sam over the shoulder of the girl and waved to him. Sam was surprised, Dean usually wanted him to stay away when he was talking to a girl. 

“Hey Sammy.” Dean said and ruffled his hair as Sam came to stand by him. 

“This is your brother?” The girl asked looking a little confused and disappointed. “You don’t look much alike.” She gave Sam a quick once over… Sam was short, he hadn’t had a growth spurt in a couple years and he did have a few too many pounds but both their dad and Dean had said it wouldn’t last long, it meant he was probably going to grow taller soon and even out. Dean, in the last few months, had grown from about five foot eight to six foot one. Dean had never been chubby he started developing muscles at about the age of ten, he’d always been solid muscle. “He’s cute I guess.” She said. Sam leaned back against the building and looked at his feet, the girl already forgetting his presence. She started looking up at Dean again with eyes scanning over him and she bit her lip in pure pleasure. 

“I’ll see you in class tomorrow.” Dean grabbed Sam and pulled him along. The girl waving and giggling. 

“Who was that?” Sam asked as they walked to the tiny, run down house they were renting for nearly nothing, no motel in the town. 

“I don’t remember her name, she’s hot, but definitely not cool.” Dean replied. Sam smiled, his brother many seem extremely shallow on the surface but once you got to know him, you would realize that underneath all Dean’s attitude, confidence and sarcasm, he was very deep and intelligent, even though he hated school and didn’t do much work. 

“So you aren’t going to hook up with her?” Sam raised his eyebrows teasingly. 

“I don’t know yet… I still might, did you see her boobs?” Dean grinned down at Sam and Sam felt his face turning red… He couldn’t wait until he stopped reacting like that when Dean talked about girls and sex. As soon as they walked in the door, the phone in Dean’s pocket started ringing…. Dean pulled it out and answered it. It could only be their father, Bobby Singer or Pastor Jim. Sam wasn’t sure how they were paying for a phone, considering all the things in their lives but somehow their dad made it work.  
“Hello.” Dean said into the phone, “Hi Dad… …We just got home.” “School, same as any other. Okay. Yeah, Okay.” Sam wasn’t getting much from Dean’s end of the conversation. “Bye.” Dean turned to Sam, “He’s working on the case farthest away and he will work his way back here, so he’ll be gone a couple of weeks.” Sam just nodded in understanding and they set out to do their homework, well, Sam did, Dean stretched out on the couch and opened a book but was really thinking of something else, probably the girl with shiny brown hair and the biggest boobs Sam had ever seen on real live teenage girl. 

 

Dean’s mind couldn’t concentrate on the homework, Dad wasn’t going to be back for a couple of weeks… which meant the little money dad had left would have to last and he’d have to stretch what they bought in groceries, unless he could convince people to let him do odd jobs for them… he couldn’t really get a job because by the time he got hired and started working, they’d be moving again. Dean would never let Sam go hungry. Dean thought back to the times he was asked to do things to other men for money and he had refused… he was not going to stoop to selling himself to random a guy in truck stop to pay for food. He’d rather steal it… but last time that didn’t go too well. Dean was never going let that happen to Sammy, he should never have to know the dirty feeling of getting checked out by guys as old as dad, but filthy and rude. There had been one time when Dean had almost done it… the man was wealthy, clean and handsome. But Dean guessed he wanted more than just a blow job. Dean was secure enough in his own sexuality to know when another man was handsome, he didn’t judge anyone for being gay or bi or whatever, in fact he found it a bit flattering that time, to have a man of good status find him attractive. 

The first-time Dean had been propositioned was at the age of eleven, a year younger then Sam is now. Dad was getting seven-year-old Sam to use the bathroom before they got back on the road at some diner. Dad had left the bill and money with Dean. Dean had paid the waitress who was in her thirties or forties and called him Handsome (but not in a creepy way but the way waitress’ do to keep up a good atmosphere) and was leaning against the counter waiting to leave. 

“You have a nice mouth, Kid.” A gruff voice said next to him. Dean turned and gave the guy a confused look but didn’t say a word. “Shit and if you aren’t the prettiest boy I’ve ever seen.” Pretty, a word that would grow to haunt Dean’s senses. “Look at those chick eyelashes… and big eyes, they’re so damn green.” Dean still didn’t say anything. “You want to earn a few bucks, looks like you could use it judging by how worn those clothes are.” Dean physically perked up and the guy took it as an invitation. “You could wrap those pretty lips around my dick and suck for $20.”

“No.” was all Dean said and looked toward the bathroom. 

“Kid, okay, how about $30.” 

“No.” 

“I’m hard as fuck because of you and now you won’t help me, which would help you.” 

“No.” Dean said again. Even though he wasn’t big, he was strong he knew he could take down this guy if he needed to. 

“You leave that boy alone.” The waitress said to the man. “Get your ass out of here, you disgusting man.” He man glared at her and left anyway. It didn’t seem like the first time he’d been kicked out of there. Dean turned and smiled at her in Thanks. “You really are a handsome kid, keep your head cool like that all the time and guys like that shouldn’t be a problem.” 

“Except my dad says I have a smart mouth… so I’ll probably say something stupid sometime.” Dean replied honestly. The waitress smiled at him. 

“Be careful out there, Honey.” Just then Sam and Dad came back and Dean let out a big breath and shook his shoulders like he was letting go of the looks that man had given him. 

No, Dean did not want that to happen to Sam ever, so Dean kept a close eye on him. Sam, at the moment, was awkward and lucky for Dean he was the only one still getting propositions like that. In fact, three days ago in the bathroom at a truck stop some guy asked Dean to fuck him hard against the wall for $100. Dean said no. Then the guy bluntly said, “Yur too purtty, must be worth a lot, ain’t ya, ya probly get with rich guys. Won’t look at us.” Dean just looked at him.

“I don’t get with men: I don’t get with anyone for money.” Dean said honestly.

“With them cock sucking lips?” The guy commented. It’s not like Dean hadn’t heard it before. He’d been hearing other guys tease him in the locker rooms at all the different schools he attended, called him Pretty Boy, and other things. Not that any school mates ever propositioned him but he was tall, strong, and they needed something to make him seem less intimidating and they got that, by Dean’s own pretty face. It was curse and a weapon at the same time. It made adults think he was charming and he could talk his way in or out of any situation, girls love it (and he loves girls), they loved his long eyelashes and freckles and big green eyes and his sandy blond hair. However, as a Hunter, it got him little respect and all that unwanted attention. Sometimes he hated being pretty. 

“I’m done.” Sam looked up from the table and noticed Dean hadn’t done any work. The smile faded from his face and turned into a critical frown. “Dean you are so smart, why don’t you just do the work and prove it.” Dean sighed, he had this conversation with Sam before and didn’t want to again, so he got up and started making dinner.


	2. Chapter 2: Halloween Make Up

**Summary for the Chapter:**

> Disclaimer: I don’t own Supernatural in any way, shape or form, no copy write infringement intended.
> 
> Author’s Note: We know from the show that Sam was a short and chubby 12-year-old, so please keep that in mind for this story as Sam is 12 and Dean is 16.
> 
> Summary: Sam is sometimes in awe of his big brother and other times jealous of him. Dean hates the way looks, except when it comes to the way hot girls look at him
> 
> Chapter summary: Dean's lips and eyes accentuated make him even prettier and it worries Sam. But Dean uses it to his advantage and can handle anyone that questions his toughness.

Halloween was fun for Dean and Sam, but they didn’t get as much out of it as many kids their age, they understand what real nightmares meant, what it meant to face monsters. However, Dean still liked to get into the spirit of things and convinced Sam they should dress up for school, something subtle and cool. With what they knew about a Vampires, they tended to dress in a mix of punk and goth. So, Dean pulled out Black T-shirts and jeans for both. They had these black leather cuffs that one of Dads’ hunter friends had made them but didn’t wear them often but the strapped them on their wrists. Dean had gone shopping the day before and pulled out the fake fangs, he’d gotten the good ones that you could actually speak with. They slipped on over your canine teeth. Then he pulled out something that surprised Sam, some eyeliner and fake blood. 

“Dean? What are you planning on doing with eye make up?” Sam questioned his big brother.

“Dude, we need it to look the part.” Dean pushed Sam down on the chair and looked him in the eyes and brought the black pencil close. Sam leaned back.

“Don’t poke my eye.”

“Chill, Sammy. I study girls like you study for school, I’ve seen them do this a thousand times. I got it.” Dean gently slid the pencil over Sam’s eyelids and under his eyes. Sam concentrated on Dean. He looked at Dean and saw that the fans made his already nice face even more defined. They accentuated his cheekbones and jawline. Sam respected his brother’s toughness and general badassery but there were times he was just too pretty. “All done.” Dean held up a mirror for Sam to look at himself and Dean had done a good job. Sam noticed that today, his eyes were closer to the color of Dean’s then they usually were. Sam had eyes that changed color, they were brown one day, gray, they blue then green but his green was more olive then Dean’s. Dean’s eyes were bright and the color of Green Apple candy. He envied them, they always sparkled with mischief. He also admired Dean’s long eyelashes… girls seem to love them too, like they were jealous of them or something.

“Thanks, Dean.” Sam started to get up.

“Hold on.” He shook the bottle of red goo and pushed Sam back down. He covered his right hand in plastic glove and squirted some out on his finger, he smeared it on Sam’s lips and put little droplets on the sides of his mouth. It was to look like he had just fed. Dean really is a genius. Sam looked again and it did look like blood, like he’d just sucked someone dry. Sam smiled up at Dean. Dean smiled back. Dean turned and had Sam hold the mirror up so he could do his own make up. Sam studied Dean… he was sorry for anyone who had to be around Dean in class, they would not get anything done. The black T-shirt he wore was tight, it showed his muscles by clinging to them. His broad shoulders looked as though they would bust out like Hulk any second. As Dean finished his eyeliner, Sam chocked. Dean’s eyes were now even more prominent then before, if that was even possible. Dean did is lips the same way he did Sam’s but it only made his pouty lips look even more ridiculously pretty. How could Dean stand that, being so pretty… it would drive him crazy but he wanted to be so badly at the same time. 

“Dean, um, are you sure you want to go out like that?” Sam hadn’t meant to say it out loud but out it came. Dean looked at him curiously.

“What, I fucked it up?” he asked.

“No.” Sam said. How was he supposed to tell his big brother he looked too pretty to go out in public. He knew guys at school teased Dean about it already, even though they respected him, it was just something to rag on him about as boys do. But today… it would be worse, not that Dean couldn’t handle himself.. it was just… he was too pretty.

“What then?” Dean folded his arms and the shirt threatened to rip. 

“Have you seen yourself?” Sam asked. “you are going to get called Pretty Boy again.” Dean swallowed hard he didn’t know Sam knew about that. Good thing he didn’t know about the strangers in random places. 

“I know.” Was all Dean said. He grabbed his back pack and threw Sam his and they headed out the door. 

Dean tried to ignore what Sam had said. He didn’t want Sam to know it bothered him. But as soon as he got to school he regretted the decision to put make up on. It had made his little brother look touch and scary. Something the kid needed. But Sam had been right… Dean looked, well not tough and scary. Right away girls surrounded him and he felt better because this was like a force field of protection from guys who wanted to tear him down… not that they could beat him up or anything Dean could handle himself in a fight… it was the taunts that got annoying. 

“Hey ladies.” Dean smirked. “Who wants to be bitten first.” He bared the fangs and they giggled he put his arms out and two girls ducked under quickly and he set his arms down on their shoulders and walked into school. Sam headed to class somewhat unnoticed. A few kids looked at him but since it was Halloween a lot them were dressed up but they noticed Sam at least. That was a first. 

“Hey Dean.” A senior football player called down the hallway. Dean couldn’t remember his name and honestly didn’t care. 

“Yeah.” He absently said as he leaned against the wall waiting for Sam. It was the end of the day and he’d made it out with only a few comments that were geared toward him, one from his English teacher even. It was part of a lesson on poetry so if fit but she didn’t have to look at him when she read the poem. Which made everyone look at him.

“You want to earn some extra money tonight.” The jock was bold. Dean wasn’t sure where this was going. He seemed like a guy whose family owned a farm or something and they needed as extra hand for chores. Dean turned and raised an eyebrow. “I know a place about an hour’s drive that men go to pick up sweet looking guys like you and they pay big bucks.” 

“I’m not gay, not that there is anything wrong with it, I’m just not.” Dean said honestly.

“Does it matter? I mean you clearly need the money.” The jock looked him over again. “And I can guarantee you would be the best-looking guy there, easy, could make a couple thousand.” Dean looked surprised. He didn’t believe for a second he would make that much; he wasn’t that pretty or was he…. He shook his head no.

“No, I don’t sell myself, not for anything.” Dean seethed. “I would never stoop so low. Not even if my brother was starving… I would make a fake charity and risk jail time if I got caught then do what you are suggesting. I am not a piece of meat; I am not weak.” Dean’s fists clenched, making his pecs jump under the tight material of the shirt. 

“I got it.” The jock backed off. Dean went back to leaning against the building. He closed his eyes and swallowed hard. He heard a gasp and looked to his right where it had come from. A group of girls around Sam’s age were staring at him. He smiled and they giggled uncontrollably. Dean sighed… girls that age are so adorable. He flexed his muscles on purpose as he shifted his weight… he knew they were just watching him and he thought it would be fun to show off for them a little. 

“Oh my God, he’s like a model…” he heard one say.

“Isn’t he that new boy, Sam’s, big brother?” 

“I think so… maybe Sam will grow up and look more like him.” Dean hadn’t realized girls didn’t like Sam. Sam had the sweetest eyes that could change color, very cool. His hair was soft and he had a sweet smile. So, he was in a physically awkward stage at the moment. He was still cute, at least Dean thought he was. But maybe he was bias, he always had a soft spot for Sam, he was the best little brother ever.


	3. Chapter 3

Chapter 3  
Dean slid in his seat just as the bell rang that boy was almost late every day. Yesterday he had walked in as the bell went off. Ms. Thomas was a younger teacher, had only been teaching for ten years. Most of the teachers here had been teaching since the 1940s. In her ten years, she’d see a lot of good looking kids pass through her class but none like Dean Winchester. He had an interesting aura around him, he is flirtatious but not immature. He doesn’t talk much in class. He stays in the back, doodling symbols of some kind. He does well on tests but rarely does homework or takes note. He is not dumb or slow just seems to be one of those kids who doesn’t like to do the work. He does enough to pass, when he does turn in an assignment it’s perfect. Dean is clearly a tough kid who has had a hard life, she noticed he protected his brother fiercely and really anyone who needed it. He never started fights but he ended them quickly. He walked with ease and confidence yet he seemed mysterious and a little dangerous… but also sweet and caring.  
“Dean, could you stay after class, I need to speak with you.” Ms. Thomas said as the students were filing out. He sighed and rolled his eyes. He looked annoyed or maybe just bored. Who knows how many times this has happened to him in his life. Dean stood in front of her, arms crossed. He was a tall one and she found herself looking right into his chest. She looked up at him, he was looking down at her with his bright green eyes. She couldn’t help but smile. “Dean, you do so well on your tests, I mean really well, best in the class, when you do turn in an assignment, it’s perfect. Why don’t you do all the work, it would be good to show on your records how smart you are.” He shrugged and sighed again.  
“I appreciate that you care, but we’ll just be leaving again anyway so I don’t see how it matters what grades I get as long as I pass. I have a nerdy little brother who takes school seriously and gets pissy and annoying every time we move, I don’t want to get attached or stand out. I just want to get by.” That was the most she had heard him speak, his mumbled answers when she called on him randomly were usually it.   
“I can understand that.” Ms. Thomas leaned back against her desk. “But if you want a scholarship to college it would be easier if you’re grades matched your true abilities.”  
“I’m not going to college.” He looked down at his shoes. “I can’t. But I am going to do everything I can to make sure Sammy gets to go.” She saw just how long his eyelashes were and how the brushed against his lightly freckled cheek. She knew he sometimes got mildly teased for being pretty, but no one dared really going at him, he could look downright scary if he wanted to.  
“That’s too bad, I have talked to your other teachers, they feel the same way I do. We all wish you would do all your work, we would love to see it.” Dean looked up again and smirked.  
“Well there is one thing I like to study and I’m always a great student.” He winked and licked his lips. Ms. Thomas rolled her eyes and laughed.   
“Don’t you dare flirt with me, I’m almost 20 years older than you and I’m your teacher and I’m not interested.” Ms. Thomas was flattered, she may see his attractiveness but her days of being attracted to a teenager is long gone. “Besides don’t you have a thing with Anna Ling?”   
“We did, but she didn’t like my attitude about meeting her parents… but I will never forget her.” He paused and looked quizzical. “I know it’s rude to ask but I was wondering how old are you exactly?”  
“It’s okay, I am not one to find that question rude. I am 32.”   
“That’s only 16 year’s older, you are 20 years older than my brother.” He paused. “I was going to guess about 25… you don’t look 32. I knew it wasn’t your first year teaching, you have too much confidence for that.. I thought maybe like you’re third year or something.”   
“Well thanks, I think.” Ms. Thomas sighed. Like Dean being teased for being pretty she was teased about her baby face.   
“Thanks for being a great History teacher. You make it fun, like listening to folklore and stories of the past but it’s all true. You even know about the stuff that the history books leave out or change, you give us the real history, thanks.” With that Dean hurried out. He didn’t want to know what happened next, he didn’t like being known for being nice. He hoped no one had heard him. He had a badass reputation to protect.  
Sam had study last period and Dean was making up a missed PE class, he had skipped one day last week to make out Anna Ling, who dumped him two days later. Sam thinks they did more than make out. Anna was the girl Sam had seen with Dean shortly after they came here, the one with long dark hair and big boobs. She wanted Dean to meet her parents. Dean said no he didn’t do parents… and well it lead her to get made. Dean didn’t seem to mind though. Sam decided to get a pass from his teacher to go to the gym and work on his homework in the bleachers and wait for Dean there. A lot of kids who had study hall last period would either go to an art, music or to the gym to hang out. The PE class at the end of the day was always mostly jocks who took would head to straight to practice afterword. The teachers kind of let them do their own thing and were really there for keeping the peace and safety. Today a game of basketball started. It wasn’t Dean’s best sport but he could get by. Dean should be on a baseball team, he was really good but they were never in one spot too long. Dean was on the skins team and the girls in the bleachers were drooling over him. Sam sighed and worked on his math homework. He couldn’t help but overhear the girls talking about his brother.   
“Anna said he’s perfect in every way if you know what I mean.”   
“Yeah, big and skilled.”   
“Damn, look at his back and the way it ripples….”  
“His eyes are so dreamy… and those lips are pure sin…”  
Sam slammed his notebook shut and moved to the other end he doesn’t need to hear all this again. That’s when he froze, he heard a senior guy sitting behind him comment on Dean and Sam didn’t like it, not at all. The low voice said… “Dean is pretty, so pretty, like a girl, I wouldn’t mind having him suck my dick.”   
“I wonder if he’d do it.” His friend said. “I heard he is good with his mouth from Anna.”  
Just then the final bell rang and Dean went in to change into his street clothes. Sam waited by the locker room door. The boys that had sat behind him were waiting too. As soon as Dean came out. Sam pulled him along saying they had to get going because he had a lot of homework. Dean followed being the big brother that he is. Sam had to talk to Dean but didn’t know how.


	4. Chapter 4

Chapter Four  
“What is wrong Sammy?” Dean pulled back as they exited the building. He was stronger so the pull halted Sam in his tracks.   
“We need to keep moving, I have to talk to you about something, but at the house, not here.” Sam looked around hoping no one would catch up to them.   
“Okay, I will listen when we get home, in the meantime… let go of sleeve.” Dean looked down where Sammy was white knuckling his shirt.  
“Oh, sorry.” Sam looked a bit ashamed and Dean lovingly put him in a head lock as they continued their way.   
They came in the door and Dean threw down his back pack and stretched out on the couch, Sam sat in the chair next to the couch and put his bag down gently on the floor. Dean looked at Sam with surprise normally he went and started on his homework at the kitchen table. This must be serious.  
“Dean….” Sam started. He wasn’t sure how to say this, it was something he knew Dean wouldn’t like. “I overheard something today and it made me feel creeped out…” Sam looked at his brother and saw that he was still relaxed even though he had a concerned look on his face. He looked anxious for him to keep going. “I overheard guys talking about you in a very sexual way, not that being gay is wrong or bad, it’s just the way they said it, the way they looked at you… it was more than just appreciatory glances or whatever. They wanted you to give them blow jobs…. said you were as pretty as a girl….”

“I know.” Dean replied. Sam looked at him with a face filled with concern and confusion. “I have heard that a million times before.” Dean looked ashamed. “I didn’t want you to find out… I don’t want you to have the completely dirty feeling that comes along with older, dirty, men making you offers for services…” Dean admitted he closed his eyes for a second like it hurt coming clean about what has happened to him. “They guys at school, they are a bunch of talk… they don’t do anything but tease me about being pretty, like I’m not aware of it enough. It’s the men in the truck stop bathrooms, or other hunters make comments when I play pool that make it creepy, that make me feel like I’m not worthy of being a hunter, they say I look to delicate, I’m a liability or only good for bait.” Dean couldn’t look at Sam this was his biggest shame, being too pretty and realizing there was nothing he could about it.   
“Dean… men have asked you to…” Sam started.  
“Yeah… all the time.” Dean sounded defeated. “I’m sorry, Sam. I’m not the big brother you need.”  
“Have you ever...?”   
“NO. I would never sell myself, Sammy, never. That’s why I’m a bad brother, I wouldn’t even if you starving.”   
“That doesn’t make you a bad brother, Dean, that makes me respect you even more. You obviously know you’re pretty and don’t let anyone take advantage of that. It takes courage to say no to money we need. If I looked like you, I don’t know if I would say no.”   
“What?” Dean looked over at Sam, who looked down at his shoes.  
“If I looked like you, I would use my looks any way I could.” Sam confessed.  
“I don’t want you to ever think that looking like me is a good thing. Sure it gives me some advantages, but mostly it sucks. I would rather look tough, if anything, I would prefer ruggedly handsome, at least then I would be respected.”  
“Dean, I don’t know what to say…”  
“There is nothing you can say… just ignore what you hear about me and my girlish face and cock sucking lips and shit like that.” Dean sighed and rolled over.   
“Can you?” Sam asked.  
“What?”   
“Ignore the comments.”  
“I try, Sammy, I try.” Was all Dean said as he was now looking at the back of the couch. He didn’t want Sam to see him cry so he pretended to sleep.


	5. Chapter 5

Chapter 5  
Dad had come back and they had moved once again, now it was just after Thanksgiving and being far north of the Mason Dixon line, like practically in Canada, the snow was already heavy on the ground. They were about the enter the fourth, no fifth school of the year and snowflakes were sticking to Dean’s long, thick eyelashes and he was blinking like crazy to knock them away.   
“Fuck.” Was all Dean said before opening the doors to the school as a wind gust blew around them sending a chill around them and Sam shivered as he laughed at Dean’s predicament. “Shut up, Sammy. It’s not funny. Told you, you don’t want to look like me.” Dean said with fake anger as he continued to blink the flakes away. They entered the school and the warmth surrounded them. It was the first time in a few days they felt good, functioning heat. The shit hole of an apartment they were renting had only a partially working heating system and they weren’t allowed to set it above 60 degrees, otherwise they wouldn’t be able to afford the heating bill. Dean was glad, Sam could be warm for a good portion of the day.   
Sam watched as people reacting to them, well to Dean, anyway. The girls giggled and waved or bit their lips and eyes widened and guys glared at him as if his existence was his own pretty self’s fault. The sign just inside the door had an arrow and the word “office” written on it. The brothers made their way in that direction. Once inside the office Dean took it upon himself to smile at the young office professional sitting behind the desk. She held her composure but blushed a little when Dean leaned on her desk asking if they could get their schedules quickly because they were new and didn’t want to be much of a bother. Dean was laying on the charm pretty thick. Sam didn’t know if he should be embarrassed or proud. The principal walked out of her office and motioned for them to come in. She stood with a strong presence and Dean straightened up. He recognized former military when he saw it. Sam immediately stood straight and walked the few steps with precision. They boys stood at attention until they were told to sit.   
“Well, Dean and Sam Winchester. It seems you move around a lot, but not in any pattern I recognize and from your stance you were raised in a military home… please explain.   
“Yes Ma’am.” Dean began. “Our father is a former Marine and when his job as a mechanic grew to be a sales representative for a parts company, he couldn’t leave us at home alone, so we travel with him.” Dean could seem like the most obedient soldier when he wanted to.  
“You mother couldn’t look after you?” The principal asked.  
“No Ma’am, she died in a house fire when I was a baby.” Sam said using the puppy dog eyes that Dean said could get him anything he wanted. You could see her eyes wavier.   
“Well, boys, you both have impressive records in the most opposite ways… Sam keep up the good work and Dean, no fighting and keep you grades up.” She said.   
“If you notice, I don’t start fights, I end them.” Dean smirked. Sam wanted to hit him, you don’t say that to the principal, especially former military. She laughed and shooed them out of her office. They received their schedule from the young woman who was probably somewhere between 22 and 27, too old to be eyeing Dean the way she was but Dean winked at here and she giggled. They split ways and each headed to their own class. Dean to 11th grade English and Sam to 7th grade Social Studies. The day was uneventful for Sam, he was asked to tell the class about himself in every period and didn’t say much and tried to act more cool and suave like his brother but he just wasn’t good at it. At the end of the day he went outside to meet Dean in the cold snowy weather when he came upon Dean, not alone, already making out with a blonde girl. Sam rolled his eyes and sighed. He didn’t really want to wait in the cold but he didn’t want to interrupt his brother…. So he acted like he just came out of the building and called his brother’s name.  
“Dean” He looked one way and then heard a giggle and a sigh from a girl.   
“Over here Sammy!” He heard Dean’s voice a little husky and low. He turned back toward where he saw them a few seconds a go.   
“Oh, sorry.” Sam said.   
“No it’s cool, this is Addison, she’s coming home with us. You got homework, right?” Dean asked and winked at Sam. Sam blushed, Dean usually conducted his sexual greatness elsewhere then where they were staying but every once and a while Sam was subject to hear what was going on in the next room. This was going to be an interesting afternoon.

**Notes for the Chapter:**

> Hey sorry so long for the update: I was very busy and had this really weird flu for a couple of weeks. I don't even know if anyone is really enjoying the story. I don't want it to become one of Wincest, but it seems like it's heading in that direction. I am debating if I Addison invites Sam to watch or not (Sam would be admiring them both)... if you have a preference feel free to let me know.


	6. Chapter 6

Chapter 6  
On the walk home Dean put his arm over Addison’s shoulder and they walked huddled together, whether it was for warmth or other purposes Sam didn’t know. He wanted out of the cold not that the place they had would be much better but still. Sam heard Addison giggle and Dean kiss her cheek or ear lobe, he really couldn’t tell. As soon as they got to the apartment Dean ordered Sam to stay in the kitchen and do his homework and the two older teens headed to the back of the apartment where the bedroom was. Sam took a deep breath and put the radio on so he could hear it. It didn’t stop him from hearing shrieks and moans from the other room but it helped. Sam finished all his homework and Dean and Addison hadn’t come out yet. He had looked up the average length of time a sixteen-year-old male could last in bed and Dean seemed to exceed it by at least four times. He closed the last book as the door in the back room opened. Dean came out and grabbed a couple glasses of water and he noticed Sam turning all kinds of red.  
“Sammy, what’s wrong?” Dean asked as he sipped from one glass. Dean was naked, not that Sam hadn’t seen him naked before, they are brothers, he’s just a sight to behold naked. Sam was still thinking about the length of time and the sounds… his older brother must be as good as they all say.  
“Um… how much longer are you going to be, I’m hungry and I’m done with my homework.” Sam asked shyly looking away.  
“Shit.” Dean said looking at the clock. “I didn’t realize we fucked for that long.” Dean turned and Sam couldn’t help but notice Dean’s ass… it was nice, he thought… He sighed and looked at his hands. Sam wasn’t some kind of freak who wanted his brother in a sexual way he just admired what his brother had, but he still felt wrong. “Addison, it’s after six.” Dean called in to the blonde. Sam heard a string of curse words come from her mouth, much less pleasure filled then the ones a little while ago. She ran out with a bundle in her arms as she drank down the water. Sam’s ears were now burning red. He didn’t mean to look at her, he also didn’t realize she’d still be naked. She looked over at Sam as she sorted through her pile of clothes.  
“It’s okay kid, you don’t have to be shy you can look.” She said. A girl, an older girl, noticed him… that was a miracle, but even more so with a naked Dean standing right there. Sam turned his face toward her but could only glance but he saw everything his whole face, neck and back felt hot and he put his head down on the table. He could feel Dean’s smirk on the back of his head. “Awwahh, that’s so cute.” Addison said of Sam’s embarrassment. Sam’s flushed skin was probably dark purple by now how much heat was headed there… he was really glad the blood hadn’t flowed to another area that would have been worse, not that he had that problem too much yet, he was still in mostly a blusher not a boner phase. He heard he clothes being pulled on and she and Dean were whispering to each other and Dean kissed her again and she left. Dean sat down and felt Sam’s forehead.  
“Dude you’re feverish.” Dean laughed a little. Sam knocked his hand away. “What’s the matter, not ready for that, a naked woman…” Dean teased. Sam swallowed hard. “Come on, what big brother would let their 12-year-old geek of a brother see their first naked girl?” Dean nudged him a little. Sam smiled a little, his brother was one of a kind. “So, what did you think?”  
Sam’s face reddened again and he just nodded. Dean rolled his eyes and stood up and put his junk in Sam’s face.  
“Dean,” Sam turned away and pretended to be offended.  
“Shut up. Sammy.” Dean messed Sam’s hair playfully and went to put clothes on. Sam just put his head down again and took a deep breath. “So what do you want for dinner?” Dean called from the back room.


	7. Chapter Seven

Chapter Seven  
So sorry it has been almost two months since my last chapter, I was dealing with personal shit.  
Sam was set, he was ready. He had been chosen as a peer tutor and his first session with a fourth-grade girl needing help with long division was about to start. A small redheaded girl who looked entirely depressed walked into the library. That must be her she was looking around, she skimmed over Sam and his table but kept looking. Sam cleared his throat and smiled as he called the name written on his sheet.   
“Katherine” She turned her head and walked quickly over to him books clutched to her body tightly. She sat down and looked more terrified then Sam had ever seen anyone. “I’m Sam, it’s nice to meet you Katherine.” She tried looking up but it seemed like she couldn’t. She tried to hide her face. “What is your assignment? Let’s get started.” Sam tried to encourage her. She pulled open her assignment book and her math book so Sam could see and she pulled out three sharpened pencils and lined paper. “Good you are very prepared. Okay show me how you solve a problem and then I can figure out how to help you.” They worked for a half hour and Katherine was slowly getting it. She was mostly having a problem with decimals and how they lined up in the problem, it was just like it was too much for her eyes and she had trouble lining things up. Suddenly a chair was turned backwards and someone was sitting staring at them. Sam looked up, it was Dean. “Sorry Katherine I have to go, my brother is here, we’ll pick this up tomorrow.” Sam said but it wasn’t heard the shy, quiet girl was staring at Dean and blushing. Sam rolled his eyes, nine years old wasn’t too young for a girl to be charmed by Dean’s looks.   
“Hey Sammy, who’s the pretty little thing?” Dean smiled at her and she nearly fell off the chair. Sam sighed. “Dean this Katherine, she’s a fourth grader I am tutoring.”   
“Hi Katherine, love the red hair.” Dean winked at her and she blushed even deeper.” Katherine was frozen. Sam picked up his books and tried getting her attention but nothing. The brothers left the girl sitting there as they walked out. Sam nudged Dean in the ribs hard. “What?” Dean looked down at his little brother.   
“She’s nine, dude, don’t flirt with her. That’s creepy and disgusting….” Sam started.  
“I was not flirting… she is a cute little girl. What is wrong with telling her that.. besides in 9 years she’ll be 18.”  
“And you’ll be 25…. “ 18 to 25… saying it like that didn’t seem like such a big difference… like 22 to 29 or 30 to 37. So it was only creepy now. “And she is so shy, she didn’t even say a word today. You never know, dude, she is probably doing home to write in her diary how she is going to marry you.”  
“Or you.” Dean said. Sam looked confused and raised an eyebrow. Dean sighed. “You are only three years older then her… she could think the same as she does for me for you in time.”  
“No, I’m short and kind of chubby kid who does all his school work. I will never have an effect on girls the way you do. “  
“Sammy, you don’t know that yet, you’re only 12.” Dean chuckles.  
“Well I have some stuff to catch up on… you lost your virginity at what 13?” Sam half-heartedly joked.  
“No I was 12.” Dean smiled. “And she was 16.” He seemed to be looking back on the memory fondly. “I was barely getting boners then and it didn’t last long but she said I was good, a fast learner.   
“I don’t’ need to hear this.” Sam covered his ears as they continued home.  
The next day he got a “Hi” out of Katherine and she worked hard again and Sam was so proud when she finally did one completely on her own and got it right. Sam beamed happily at her and she smiled back. Dean was right she was a pretty little girl, she would grow up to be a beautiful woman who wouldn’t give Sam the time of day. Sam could hit himself, why did he always to that self-doubt place? He didn’t mean too. It just always happened… he decided to blame it on the pre-puberty hormones. Katherine did a few more problems on her own and they were perfect. “Nice Work Katherine.” Sam said.  
“Thank you Sam, you made it easy to understand. I could not have done this without you.” A full sentence, a full two sentences had come out of her.   
“What couldn’t you do without my brother?” Dean asked as he sat down.   
“Uh…” Katherine just started at him again.   
“She just answered five long division problems with decimals, correctly on her own.” Sam said proudly.  
“Awesome.” Dean smiled at her and grabbed her hand in support and she started blushing like crazy again. “Congratulations.” Then he pulled off one his friendship bracelets that he had a ton of because girls make them for him. He slipped it on her wrist and tightened it. She just looked at it sitting there on her wrist. It was like she was in shock, she couldn’t believe that such a gorgeous teenage guy gave her a bracelet.   
“Th… Tha… Thanks.” She mumbled out as they packed their stuff up into their bags.   
“You are very welcome.” Dean smiled big at the girl, she just blushed a nearly purple color. He leaned down and kissed her cheek. “Math is hard, you deserved a reward but my little bro didn’t think to bring you one so that’s for you.” Katherine was once again frozen unable to move. Sam and Dean walked out of the Library out of the school and to the Impala.   
“You’re terrible. You are horrible, what are you doing to that poor girl?”   
“Sam, calm down, she needed confidence, you helped her with skills, I gave her confidence, she’ll ace that test.” Dean was relaxed behind the wheel, it was a miracle Dad had left her for them to drive. Sam realized, Dean wasn’t wrong… how he treated Katherine was how Dean would treat a little sister if they had one.


	8. Chapter 8

Two days after the Katherine situation Dad was back and they were on the move again. They had been driving all day and were now stopped for fuel for the car and themselves. Dad was filling up the tank and sent the boys into the diner next door for food. As soon as they walked in the glances Dean got began right away. A young waitress saw him and nearly dropped the tray of food she was carrying. The mom and daughter in a booth both looked him up and down and seemed very pleased… Then there was the big trucker in the corner with a long beard and a round belly. He was tall, taller then dad by a few inches. He looked gruff and mean. He was eyeing Dean up and licking his lips. Sam nudged Dean and whispered a warning to Dean.  
“Dude, I know, I could feel his stare. We are just going to order food and get the hell out of here okay.” Sam nodded and Dean leaned coolly against the counter and the woman behind it looked up a little annoyed at first but then softened at the sight of Dean’s pretty face. “Hey Nancy” Dean smiled his flirting smile as he read the name tag on her uniform. “Could we get six burgers and some fries to go?”   
“Sure thing, Handsome.” Nancy said as she turned to place the order with the cook. “You two growing boys hungry?”   
“Yes, Ma’am.” Dean was laying it on thick he let a bit of Southern drawl come out on those words. He was good at that, accents. He once convinced a whole school he was from London, England. Nancy nearly melted into the floor at his voice. “Our Daddy’s next door getting the tank filled up” He drawled even more seeing the reaction he got. “Can we get three large soda’s too?” Nancy nodded and began to fill up the paper cups. Sam didn’t know what to do, he just sort of smiled like an idiot. The diner smelled good and he was hungry. He had almost forgotten about the creepy trucker in the corner that is until he went by them and smacked Dean’s ass. Dean just sighed and shrugged his shoulders like it was no big deal. Sam wanted to hurt that man. No one had the right to touch anyone without their consent. Soon a bag was being passed to Dean and he paid. Same was carrying the drinks in a carrier and Dean the bag with the burgers and fries. Nancy winked at Dean as they headed for the door. Dean turned to the left and headed to the bathroom, Sam followed and Dean handed him the other bag. Sam waited by the door as listened to Dean take a leak a freaking long leak….. Dean zipped up and went to wash his hands when the big trucker came out of nowhere and grabbed Dean by the arm.  
“Hey Pretty Boy, why did you tease me out there, flirting with Nancy while I was looking at you?” He pushed Dean against the wall, this guy made Dean look so small, but Sam new just how strong Dean was. Sam would gladly jump in if he had too.   
“Hey, dude, I don’t swing that way… it’s cool, but I don’t… I am sorry if you got a vibe from me, not my intention, I can’t just turn this off.” Dean smirked. The man looked amused for a split second, but then looked angry again. The man held Dean against the wall and started humping him… Sam’s mouth dropped open and he froze. Dean kneed him and punched him forcefully between the eyes. Which got the man down on his knees in pain.  
“Don’t Pretty Boy me and then try to hump my leg like a dog.” Dean growled. “Especially not in front of my kid brother.” The man looked at Sam and was genuinely surprised, like he really hadn’t seen him at all. Just then John entered the bathroom and looked at the man on his knees and at Sam holding food bags, looking shocked and Dean angry.   
“Boys, what is going on here.” John said on the edge of anger, he didn’t want to believe Dean was getting into trouble again. Sam couldn’t take it… he let it spill…  
‘That guy was hitting on Dean and humping his leg….”   
“What?” John looked at Dean and he shrugged.  
“Dad it happens all the time, older guys like him hit on Dean all the time. Dean always turns them down.” Sam kept going.  
“Sam…” Dean looked embarrassed and mad.  
“Sorry, he needs to know.”  
“I am really not surprised, other hunters have warned me to keep an eye on you, to get you scared up, to make sure you grow facial hair when you can… I didn’t want to hear it…. Ellen was right, your looks are a weakness, you might only be good for bait.”   
“What?” The boys said together in an almost rage.   
“Dean’s as good a hunter as anybody, probably better than most twice his age.”   
“I know but he’s pretty, and that can be risky….”  
“Who’s Ellen?” Of course that is what concerned Dean now, the woman as the man lay forgotten on the bathroom floor as they filed out.

Yes I’m bringing in Ellen and Jo… it goes along with Dean being pretty… I liked them.  
I wonder how John is going to continue to react to this news that what others said would happen is actually happening.


	9. Chapter 9

John swung the Impala into the dusty parking lot of a bar in the middle of the afternoon. The Roadhouse was not much to look at but was greeted with a polite smile, not one of a warm welcome but polite. The woman was about John's age with long brown hair that had some ginger tint. She wasn't tall but had a nice figure for her age. 

"Hi Ellen." John said, they didn't hug or shake hands but nodded at each other. 

"John." was all she said, she had one of those lower, raspy, sexy voices and Dean smiled his little smirk. 

"You think her and dad had a thing?" Dean whispered to Sam after they were inside. Sam shrugged his shoulders, it was possible, it's not like their dad was priest, he had needs like a normal man.

"Ellen I'd like you to officially meet my boys, Dean and Sam." Ellen turned to look at them and reached out to shake their hands. She looked them over carefully and smiled. She may be a little irritated with their father but the boys have done nothing to make her mad. They boys shook her hand and smiled politely. 

"Nice to meet you." Dean said held her hand a moment longer then he needed to. Sam wasn't sure if he was flirting or just trying to figure her out. It could be both. 

"Yes, nice to meet you boys too." She said and forced the grip of the teenage away. Sam laughed, she wasn't going to take any shit from a teenage boy no matter how pretty he was. Sam decided right then he liked this woman. "JoAnna Beth, get out here, I need you to meet some people." Ellen yelled.

"Mom, call me Jo, how many times to do I have to tell you." A voice came from a behind a swinging door and it was pushed open by a blonde girl about the same age as Sam. She was cute but Sam could tell she was just as tough as her mother. The girl walked over rolling her eyes but stopped dead in her tracks frozen when she saw Dean. Sam knew this look, this situation, he called it the Dean Affect. The girl physically shook herself out of it and walked up next to her mother. She tried to play it cool and look confident she even pulled her shoulders back to try and stick out the chest she didn't yet have. 

"Jo you remember John Winchester, right, comes in every now and then?" Ellen spoke to her daughter but her eyes were on Dean's face, probably studying the freckles, long lashes, green eyes and pouty lips. Jo nodded. "These are his boys, Dean and Sam." Ellen nudged her so she would look at Sam too. She glanced his way and then back up at Dean. 

"Pleasure." was all she said. She pushed past Dean then swinging her hips to the Jukebox and picked a song she thought might impress Dean. Dean just sort of shook his head and turned to Ellen. She looked at him with a glare, he shrugged and put his hands up in surrender as if saying, "I won't touch her or go after her". Ellen seemed satisfied with that and looked at Sam. Sam just stared blankly at her and she smiled. His cluelessness was a good sign for her. Ellen went on to tell Dean and Sam that her bar was place where other hunter's wondered through, shared stories and gave information and how she caught cases and passed them out as she saw fit. Dean was impressed, Sam was surprised there was a place like this. Most hunters he ever met seemed to stay to themselves and come upon each other by pure chance. 

Sam looked over at Jo who had been given the task of cleaning the tables and chairs but she wasn't getting much done as she was staring at Dean. John noticed and looked at Ellen. "This is why I came to you... I need help... I know it's a thing right now for boys have this hair length but I need you to cut it so he doesn't look so pretty..." John gestured to Dean and Dean glared at him. 

"I told you, he's been being propositioned hasn't he?" Ellen looked at Dean with great concern. 

"I'm right here for fuck's sake." Dean sighed. 

"Watch that mouth, Boy." Ellen scolded him. 

"Or you could?" Dean smirked. Ellen rolled her eyes and John smacked the back of head. 

"Dean, she's my age, old enough to be your mom... stop." John glared.

"Sorry, I can't turn it off." Dean grumbled. 

"You will for Jo, right." Ellen looked worried she may have misjudged his reaction earlier.

"Yes, I promise, until she is 18." Ellen still looked mad but nodded. She couldn't do anything once her daughter was a legal adult so that promise would have to do. 

"Well, then let me get the clippers." Ellen headed to a small storage closet. Sam wondered why she would have hair clippers in there... maybe because hunter's need to change appearance quickly sometimes if law enforcement caught wind of them. Dean's hair was soft and like many boys in this day and age it was down to his cheeks and parted in the middle. Not really long but long enough for those disgusting men to say they wanted to run their fingers through it and tangle it around while he was blowing them. Sam shook the thoughts away. Maybe the hair cut would help.


	10. Chapter 10

Dean ran hand through the shorter locks of his hair... it wasn't a buzz cut or anything but he looked a little sheepish until he caught Jo staring at him even harder. He casually got up and sauntered to the bathroom... Sam was convinced that is was to check himself out in the mirror not that he actually had use the facilities. What was it that Dean was going to discover... the shorter hair was going to expose his eyes more and accent the jawline that was sharp and rugged. Not to mention the freckles were more visible now. Sam just rolled his eyes and sighed. Sam didn't see how this was going to help matters any. Dean was still very much a pretty boy... hopefully he would start growing a beard soon... maybe that would take away the pretty and make him just handsome, less vulnerable. A few minutes later Dean returned and thanked Ellen and gave her a hug. Dean headed over to the jukebox himself and picked a Led Zeppelin song. Dean had a nodded his head along and played air guitar and John smiled. 

"Well, I guess he is okay with the hair cut." John said to Ellen. He laughed at his eldest too cool for you son and shook his head. 

"I don't think it's going to help, John, he's still too pretty for his own good." Ellen looked like she would like to protect Dean from the world. 

"Well, aside from purposefully scaring his face... I don't have any other way to rugged him up." John still looked worried but also happy at that moment, his sons were not in danger and he could relax there was nothing to hunt nearby. 

"You boys better head out soon, the crowd will be coming in a bit. I don't want the boys here when it does... I kick Jo out too. It's too rough and tough for the kids." Ellen stated as she looked at the time. 

"Damn, I was hoping you had that room we could stay in for the night... just getting off the road would be nice." John pleaded with her.

"I will let you stay if you keep the boys in." Ellen bargained. "You have to stay out of here too then." John looked as if this was the biggest betrayal of all time but he nodded in agreement. 

"Boys get your overnight gear, we are staying out back in the bunk room." John called. "Then after we settle in, we will go get dinner. Hey Jo, you can come with us too, if it's okay with your mom." Jo looked to Ellen with a please look and Ellen nodded, she didn't like the idea but it got her away from the bar. Jo untied the apron from around her waist and put it behind the bar and pulled her hair out of the ponytail. She looked at Dean to see if he noticed but he was already headed out the car. Sam laughed to himself and shook his head. He was also slightly jealous, Jo is his age and kinda cute and she was interested in Dean... but he understood, he was just in an awkward stage and if genetics played any role in his looks, he would grow up and have the same kind of reaction from women that his brother and father had. Yes, Sam had noticed how women looked at his father too. It was just going to be time. He followed Dean out the door to grab his bag from the back seat. They followed John around the back of the Roadhouse and to a surprisingly nice bunk room, it had a big bathroom and small kitchenette. There was a couch by a table and an old TV that did have a VCR hooked up. Then there were Two double beds and a set of bunk beds. Dean and John each took a big bed, Sam didn't care, he took the bunk beds, at least he got a bed to himself. This was a nice change from a motel. 

The waitress at the dinner was in her 20s and Dean flirted and nearly got her number until John butted in and told her he was just shy of 17. She frowned and brought the bill. Dean looked as if John had committed murder. Luckily no creepy older guys were there to try and pick up Dean. This made Sam's night, at least it was normal or least looked like they were normal. Dean had convinced John to stop at the video rental place so they could get a movie, none of them had seen a movie in a long time. They got Braveheart and Golden Eye. This would be a great evening. Dean and Sam stayed up and watched both movies that the two of them enjoyed very much. John had fallen asleep after a shower and twenty minutes into the first movie. The boys were so happy to not have anything to worry about that neither of them had the thought to sneak out. They both took a shower and went to bed after finishing the movies. It was a good night, a normal night, one Sam would remember for a long time.


End file.
